Tetrahydro-2-furoic acid
# Tetrahydro-2-furoic acid

Tetrahydro-2-furoic acid is an organic compound with the formula $HO_2CC_4H_7O.$ It is a colorless oil. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate relevant to the production of several drugs, including Terazosin for the treatment of prostate enlargement and hypertension. or high boiling liquid,

## Synthesis

Furoic acid is reduced to tetrahydro-2-furoic acid, as originally reported in 1913 by Wienhaus. Tetrahydro-2-furoic acid has been prepared via selective hydrogenation of 2-furoic acid over a bimetallic catalyst of palladium-nickel supported on alumina.

Enantioselective heterogeneous hydrogenation of furoic acid to chiral tetrahydro-2-furoic acid proceeds in the presence of cinchonidine-modified alumina supported palladium catalyst in 95% yield and 32% enantiomeric excess. Similarly, homogeneous hydrogenation to chiral tetrahydro-2-furoic acid proceeds quantitatively with 24-27% enantiomeric excess in methanol solution employing a chiral, ferrocene-phosphine catalyst.

## Applications

### Pharmaceuticals

Reaction of tetrahydro-2-furoic acid with the hydrochloride salt of 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]-propanenitrile provided alfuzosin, a drug for the treatment of benign prostatic hyperplasia (BPH).

A key intermediate to faropenem, an antibiotic for the treatment of acute bacterial sinusitis, chronic bronchitis and pneumonia has been prepared from tetrahydro-2-furoic acid via a process including chiral resolution and chlorination.

Tecadenoson is another example of a drug made using tetrahydro-2-furoic acid.

